TiCl4-mediated deoxygenative reduction of aromatic ketones to alkylarenes with ammonia borane.
Org Biomol Chem
; 22(5): 932-939, 2024 Jan 31.
Article
en En
| MEDLINE
| ID: mdl-38180250
ABSTRACT
A rapid and mild protocol for the exhaustive deoxygenation of various aromatic ketones to corresponding alkanes was described, which was mediated by TiCl4 and used ammonia borane (AB) as the reductant. This reduction protocol applies to a wide range of substrates in moderate to excellent yields at room temperature. The gram-scale reaction and syntheses of some key building blocks for SGLT2 inhibitors demonstrated the practicability of this methodology. Preliminary mechanistic studies revealed that the ketone is first converted into an alcohol, which then undergoes a carbocation to give the alkane via hydrogenolysis.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Contexto en salud:
8_ODS3_consumo_sustancias_psicoactivas
Problema de salud:
8_alcohol
Tipo de estudio:
Guideline
Idioma:
En
Revista:
Org Biomol Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2024
Tipo del documento:
Article